Water → alpha-Oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid

HRID 488333Notes

Reaction equation

HRID 488333 reaction equation
C([O:3][C:4](=[O:33])[C:5](=[O:32])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][CH:7]=1)C.[OH-].[Na+].O>CO>[O:32]=[C:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:8][CH:7]=1)[C:4]([OH:33])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54340854alpha-Oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid ethyl ester

Product 1

HCID 19091785alpha-Oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acidYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1.44 g (3.17 mmol) of alpha-oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid ethyl ester in 100 ml of hot methanol was added 3.5 ml (3.5 mmol) of 1N NaOH. The mixture was heated on a steam bath for 5 minutes, water (20 ml) was added and the solvents were removed at reduced pressure. Water (100 ml) and 7.0 ml of 1.0N HCl were added to the residue and the product was extracted with methylene chloride-THF (4:1). The dried extract was concentrated at reduced pressure to a solid which was recrystallized from acetone-hexane to give 1.14 g (84% yield, mp 98°-100°) of alpha-oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid

Workup

  1. temperatureThe mixture was heated on a steam bath for 5 minutes
  2. customthe solvents were removed at reduced pressure
  3. additionWater (100 ml) and 7.0 ml of 1.0N HCl were added to the residue
  4. extractionthe product was extracted with methylene chloride-THF (4:1)
  5. extractionThe dried extract
  6. concentrationwas concentrated at reduced pressure to a solid which
  7. customwas recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-01ad4cc0a4c64417abd899ac46606e88
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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